65933-61-1Relevant academic research and scientific papers
Photoredox/Nickel Dual Catalysis Enables the Synthesis of Alkyl Cyclopropanes via C(sp3)-C(sp3) Cross Electrophile Coupling of Unactivated Alkyl Electrophiles
Dey, Purusattam,Jana, Sayan K.,Maiti, Mamata,Maji, Biplab
, p. 1298 - 1302 (2022/02/25)
A facile synthesis of mono-, 1,1- and 1,2-disubstituted cyclopropanes via visible light-mediated photoredox/nickel dual catalysis is demonstrated. The challenging intramolecular C(sp3)-C(sp3) cross-electrophile coupling of readily available unactivated 1,3-dialkyl electrophiles was performed under mild conditions that allowed traditionally reactive functional groups to be included. Mechanistic inspection and control experiments revealed the importance of dual catalysis and that the reaction proceeds via a stepwise oxidative addition followed by an intramolecular SN2 reaction.
Cyclopropanes in Nicholas reaction: Formation of spiroketals with a five-membered and a seven- or an eight-membered ring This paper is dedicated to Professor Paul A. Wender, one of the most creative contributors to the broad discipline of organic chemistry, on the occasion of the Tetrahedron Prize
Mukai, Chisato,Kojima, Takahiro,Kawamura, Takamasa,Inagaki, Fuyuhiko
, p. 7659 - 7669 (2013/08/23)
The consecutive treatment of 5-hydroxy-1-pentynyl 2,2-disubstituted- cyclopropyl ketones with Co2(CO)8 and BF 3·OEt2 produced the corresponding Co 2(CO)6-complexed dioxaspiro[4.6] derivatives. The one-carbon homologated substrates also afforded dioxaspiro[4.7]. It was found that this procedure can be applied to the substrates with gem-disubstituents as well as a mono-aryl substituent on the cyclopropane, but the mono-alkyl substituted cyclopropanes are insufficient.
3-exo-tet Cyclization of 2,2-disubstituted 1,3-dihalopropanes with indium in aqueous and ionic liquid solvent system
Tsuchiya, Yuhsuke,Izumisawa, Yuhta,Togo, Hideo
experimental part, p. 7533 - 7537 (2009/12/04)
The 3-exo-tet cyclization of 2,2-disubstituted 1,3-dihalopropanes with In powder in THF solution of 20% H2O, dioxane solution of 20% H2O, and ionic liquids, such as [bmim]Br, [bmim]Cl, and [bmin]BF4, respectively, was effi
Radical 3-exo-tet cyclization of 1,3-dihalopropanes with SmI2 to form cyclopropanes
Ohkita, Tsuyoshi,Tsuchiya, Yuhsuke,Togo, Hideo
, p. 7247 - 7251 (2008/12/20)
The preparation of 1,1-disubstituted and monosubstituted cyclopropanes from corresponding 2,2-disubstituted and 2-monosubstituted 1,3-dihalopropanes, respectively, with SmI2 in THF was efficiently carried out. The reaction mechanism was propose
Facile preparation of cyclopropanes from 2-iodoethyl-substituted olefins and 1,3-dihalopropanes with zinc powder
Sakuma, Daisuke,Togo, Hideo
, p. 10138 - 10145 (2007/10/03)
Two efficient, simple, cheap, and environmentally benign preparations of cyclopropanes were achieved. One is the formation via 3-exo-trig manner from various electron-deficient 2-iodoethyl-substituted olefins with zinc powder in a mixture of t-butyl alcoh
Formation of cyclopropanes by the reductive coupling of 1,3-dihalides promoted by titanocene(II) species
Takeda, Takeshi,Shimane, Keiko,Fujiwara, Tooru,Tsubouchi, Akira
, p. 290 - 291 (2007/10/03)
The treatment of various 1,3-dihalides including the ones bearing an ester group with the titanocene(II) species produced cyclopropanes in good yields. The reaction of dihalides possessing two secondary halogens proceeded stereoselectively to afford trans
Breaking of the C-C bond of cyclobutanones by rhodium(I) and its extension to catalytic synthetic reactions
Murakami,Amii,Shigeto,Ito
, p. 8285 - 8290 (2007/10/03)
A study of rhodium(I)-catalyzed synthetic transformations involving selective breaking of the C-C bond α to the carbonyl group of cyclobutanones is described. Decarbonylation took place on treatment of a cyclobutanone with an equimolar amount of (Ph3
Synthesis of substituted cyclopropanes from 1,3-diols through the corresponding cyclic sulfates
Guijarro, David,Yus, Miguel
, p. 11445 - 11456 (2007/10/02)
The reaction of different cyclic sulfates 2 (easily prepared from the corresponding 1,3-diols 1 following the Sharpless methodology) with an excess of lithium powder and a catalytic amount of DTBB (5 mol %) leads to the corresponding substituted cyclopropanes 3 through a γ-elimination process, the sulfate ion acting as leaving group.
Chelation assistance in the activation of Csp3-S bonds in nickel-catalyzed cross-coupling reactions
Wong, Ken-Tsung,Yuan, Tien-Min,Wang, Maw Cherng,Tung, Hsiao-Hsian,Luh, Tien-Yau
, p. 8920 - 8929 (2007/10/02)
An unprecedented chelation approach to activate Csp3-S bonds in nickel-catalyzed cross-coupling reactions is described. Our theme was based on the formation of a chelation complex which results in the enhancement of the reactivity of aliphatic
Direct transformation of dialkyl sulfates into alkyllithium reagents by a naphthalene-catalysed lithiation
Guijarro, David,Guillena, Gabricia,Mancheno, Balbino,Yus, Miguel
, p. 3427 - 3436 (2007/10/02)
The lithiation of primary and secondary dialkyl sufates with an excess of lithium powder in the presence of a catalytic amount of naphthalene (4 mol %) in THF at -78°C leads to the corresponding alkyllithium reagents (1:2 molar ratio) which react with different electrophiles, mainly carbonyl compounds, to yield after hydrolysis, the expected coupling products. This methodology represents an indirect way to transform alcohols into organolithium compounds through the corresponding dialkyl sulfates. When the same procedure is applied to five or six member cyclic sulfates (derived from 1,2- or 1,3-diols) only products arising from a β- or γ-elimination process (giving olefins or cyclopropanes), respectively, are obtained.
